Reaction #632005

Reaction equation

tert-Butylamine

3-chloropropanesulfonyl chloride

→

desired product

Yield 99.0%

N-tert-butyl-(3-chloro)propylsulfonamide

Yield 99.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was warmed to room temperature
2. 2
   FiltrationThe mixture was filtered
3. 3
   Concentrationthe filtrate was concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe concentrate was dissolved in dichloromethane (2.0 L)
5. 5
   Washwashed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L)
6. 6
   Dryingdried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Otherto give a slightly yellow solid, which
10. 10
    Otherwas crystallized from hexane

Procedure

tert-Butylamine (3.0 mol, 315.3 mL) was dissolved in THF (2.5 L). The solution was cooled to −20° C. and treated slowly with 3-chloropropanesulfonyl chloride (1.5 mol, 182.4 mL). The reaction mixture was warmed to room temperature and stirred for 24 hours. The mixture was filtered, and the filtrate was concentrated in vacuo. The concentrate was dissolved in dichloromethane (2.0 L), washed with 1N HCl (1.0 L), water (1.0 L), brine (1.0 L), dried over Na2SO4, filtered, and concentrated in vacuo to give a slightly yellow solid, which was crystallized from hexane to provide the desired product as a white solid (316.0 g, 99%). 1H NMR (CDCl3) δ 1.38 (s, 9H), 2.30-2.27 (m, 2H), 3.22 (t, J=7.35 Hz, 2H), 3.68 (t, J=6.2 Hz, 2H), 4.35 (br, 1H).

Source